US5907333A - Ink jet print head containing a radiation curable resin layer - Google Patents

Ink jet print head containing a radiation curable resin layer Download PDF

Info

Publication number
US5907333A
US5907333A US08/827,564 US82756497A US5907333A US 5907333 A US5907333 A US 5907333A US 82756497 A US82756497 A US 82756497A US 5907333 A US5907333 A US 5907333A
Authority
US
United States
Prior art keywords
ink jet
print head
resin composition
jet print
epoxy compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US08/827,564
Other languages
English (en)
Inventor
Girish Shivaji Patil
Paul Timothy Spivey
Gary Raymond Williams
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Funai Electric Co Ltd
Original Assignee
Lexmark International Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Lexmark International Inc filed Critical Lexmark International Inc
Priority to US08/827,564 priority Critical patent/US5907333A/en
Assigned to LEXMARK INTERNATIONAL, INC. reassignment LEXMARK INTERNATIONAL, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: PATIL, GIRISH S., SPIVEY, PAUL T., WILLIAMS, GARY R.
Priority to EP98302358A priority patent/EP0867488B1/en
Priority to AT98302358T priority patent/ATE242299T1/de
Priority to CN98108878A priority patent/CN1119245C/zh
Priority to DE69815189T priority patent/DE69815189T2/de
Priority to KR1019980010855A priority patent/KR100527608B1/ko
Priority to JP12383498A priority patent/JP4051467B2/ja
Priority to TW087104671A priority patent/TW412633B/zh
Publication of US5907333A publication Critical patent/US5907333A/en
Application granted granted Critical
Assigned to FUNAI ELECTRIC CO., LTD reassignment FUNAI ELECTRIC CO., LTD ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: Lexmark International Technology, S.A., LEXMARK INTERNATIONAL, INC.
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Images

Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41J—TYPEWRITERS; SELECTIVE PRINTING MECHANISMS, i.e. MECHANISMS PRINTING OTHERWISE THAN FROM A FORME; CORRECTION OF TYPOGRAPHICAL ERRORS
    • B41J2/00—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed
    • B41J2/005—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed characterised by bringing liquid or particles selectively into contact with a printing material
    • B41J2/01—Ink jet
    • B41J2/135—Nozzles
    • B41J2/16—Production of nozzles
    • B41J2/1601—Production of bubble jet print heads
    • B41J2/1603—Production of bubble jet print heads of the front shooter type
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41J—TYPEWRITERS; SELECTIVE PRINTING MECHANISMS, i.e. MECHANISMS PRINTING OTHERWISE THAN FROM A FORME; CORRECTION OF TYPOGRAPHICAL ERRORS
    • B41J2/00—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed
    • B41J2/005—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed characterised by bringing liquid or particles selectively into contact with a printing material
    • B41J2/01—Ink jet
    • B41J2/135—Nozzles
    • B41J2/16—Production of nozzles
    • B41J2/1607—Production of print heads with piezoelectric elements
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41J—TYPEWRITERS; SELECTIVE PRINTING MECHANISMS, i.e. MECHANISMS PRINTING OTHERWISE THAN FROM A FORME; CORRECTION OF TYPOGRAPHICAL ERRORS
    • B41J2/00—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed
    • B41J2/005—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed characterised by bringing liquid or particles selectively into contact with a printing material
    • B41J2/01—Ink jet
    • B41J2/135—Nozzles
    • B41J2/16—Production of nozzles
    • B41J2/1621—Manufacturing processes
    • B41J2/1623—Manufacturing processes bonding and adhesion
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41J—TYPEWRITERS; SELECTIVE PRINTING MECHANISMS, i.e. MECHANISMS PRINTING OTHERWISE THAN FROM A FORME; CORRECTION OF TYPOGRAPHICAL ERRORS
    • B41J2/00—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed
    • B41J2/005—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed characterised by bringing liquid or particles selectively into contact with a printing material
    • B41J2/01—Ink jet
    • B41J2/135—Nozzles
    • B41J2/16—Production of nozzles
    • B41J2/1621—Manufacturing processes
    • B41J2/1631—Manufacturing processes photolithography
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41J—TYPEWRITERS; SELECTIVE PRINTING MECHANISMS, i.e. MECHANISMS PRINTING OTHERWISE THAN FROM A FORME; CORRECTION OF TYPOGRAPHICAL ERRORS
    • B41J2/00—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed
    • B41J2/005—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed characterised by bringing liquid or particles selectively into contact with a printing material
    • B41J2/01—Ink jet
    • B41J2/135—Nozzles
    • B41J2/16—Production of nozzles
    • B41J2/1621—Manufacturing processes
    • B41J2/164—Manufacturing processes thin film formation
    • B41J2/1645—Manufacturing processes thin film formation thin film formation by spincoating
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41J—TYPEWRITERS; SELECTIVE PRINTING MECHANISMS, i.e. MECHANISMS PRINTING OTHERWISE THAN FROM A FORME; CORRECTION OF TYPOGRAPHICAL ERRORS
    • B41J2202/00—Embodiments of or processes related to ink-jet or thermal heads
    • B41J2202/01—Embodiments of or processes related to ink-jet heads
    • B41J2202/03—Specific materials used

Definitions

  • This invention relates to an ink jet print head containing an improved radiation curable resin layer.
  • the ink jet print head of an ink jet printer generally consists of an orifice plate containing orifices or injection parts for discharging ink for recording on a substrate, ink passage ways connecting the orifices to an ink supply and an energy imparting device for ejecting ink from the print head through the orifices.
  • the energy for discharging the ink during recording is generated in most cases by resistance elements or piezoelectric devices.
  • Methods for making the ink passage ways for ink jet print heads include, for example, forming fine grooves in a thin layer of glass, metal, or plastic by cutting or etching and then bonding another thin layer of material onto the layer having such grooves formed thereon to form liquid passage ways.
  • Another method involves forming grooves in a photosensitive resin coated on a substrate containing the energy imparting device by photo lithographic techniques. Once the grooves are formed in the photosensitive resin another thin layered material is attached to the grooved resin to form, for example, nozzle plates.
  • the use of a photosensitive resin to provide at least a portion of the ink passage layer is more advantageous than other methods since the liquid passage ways can be manufactured with higher precision and yield and liquid jet recording heads can be obtained with better quality and lower cost.
  • the photosensitive resin is required to have (1) excellent adhesion as a cured film to a substrate; (2) excellent mechanical strength and durability, when cured; and (3) excellent sensitivity and resolution upon patterning with a radiation source.
  • U.S. Pat. No. 4,623,676 describes a radiation curable composition for use as a protective coating for a photographic element containing a polymerizable acrylic compound, a polymerizable epoxy-functional silane, a free radical aromatic complex salt photoinitiator capable of initiating polymerization of said acrylic compound, and a cationic aromatic complex salt photoinitiator capable of initiating polymerization of said epoxy functional silane.
  • U.S. Pat. No. 4,688,053 describes a liquid jet recording head having a layer of a radiation curable resin composition containing a linear polymer having a glass transition temperature of at least 50/C and a weight average molecular weight of at least 3.0 ⁇ 10 4 , a monomer having an ethylenically unsaturated bond, an epoxy resin having one or more epoxy groups, and a polymerization initiator capable of generating a Lewis acid by irradiation with an active energy source.
  • U.S. Pat. No. 4,090,936 describes a photohardenable composition containing an organic compound having an average epoxide functionality in the range of about 1 to 1.3; an organic polymer selected from polymers derived from acrylate or methacrylate monomers, copolymers of styrene and allyl alcohol, and polyvinyl butyral polymers; and an aromatic complex salt aromatic complex salt photoinitiator.
  • photosensitive resins provide all of the requisite characteristics for use in jet print head applications.
  • photosensitive resins used for pattern formation in printing plates, print wires, etc. have inferior adhesion to glass, metal, ceramic and plastic, and are insufficient in mechanical strength and durability when cured although they may have good sensitivity and resolution.
  • deformation or delamination from the substrate or degradation of the photosensitive resin layer are liable to occur during usage which reduces the reliability of the ink jet print head by impeding the flow of ink in the ink passage ways or making the ink droplet discharge noticeably unstable.
  • photo curable resins which adhere to glass, metal, ceramic and plastic, and provide satisfactory mechanical strength and durability after curing, are inferior in sensitivity and resolution.
  • the inherent characteristics of photo curable resins makes them unsuitable for use in providing ink passage ways because they cannot be cured in the precise patterns required for use in ink jet print heads.
  • An object of the present invention is to provide an improved radiation curable resin for use in ink jet print heads.
  • Another object of the present invention is to provide an ink jet print head containing an ink passage layer made of a resin satisfying all of the requisite characteristics as mentioned above, which is inexpensive, precise, high in reliability and excellent in durability.
  • Yet another object of the present invention is to provide an ink jet print head having precisely manufactured ink passage ways.
  • the invention provides an ink jet print head containing ink passage ways in a radiation curable resin attached to a substrate containing an energy imparting device for ejecting ink from the print head.
  • the passage ways are formed in the resin by subjecting a layer of radiation curable resin to a predetermined radiation pattern to thereby form cured regions of the resin. Uncured regions of the resin may then be removed.
  • the invention provides a radiation curable resin composition
  • a radiation curable resin composition comprising: from about 5 to about 50 and preferably from about 10 to about 20 weight percent of a first multifunctional epoxy compound; from about 0.05 to about 20 and preferably from about 0.1 to about 5.0 weight percent of a second multifunctional epoxy compound; from about 1.0 to about 10 and preferably from about 1.5 to about 5 weight percent of a photoinitiator capable of generating a cation, like an aromatic complex salt photoinitiator; and from about 20 to about 90 weight percent and preferably from about 45 to about 75 weight percent of a non photoreactive solvent, wherein the weight percents are based on the total weight of the resin composition, and all ranges subsumed therein may be included.
  • the resin composition uses a nonphotoreactive solvent system (which could be aqueous or nonaqueous) that is environmentally acceptable.
  • the radiation cured resin layer of the invention exhibits greater resolution, higher aspect ratios and enhanced adhesion to metal surfaces such as gold or gold/tantalum, thereby extending its application to present and projected product requirements.
  • the cured resin provides a permanently defined and high pH ink resistant barrier layer that can contribute to controlled ink droplet size in ink jet print heads while resisting corrosion or chemical attack by the ink itself.
  • the radiation cured resin also results in unexpectedly superior adhesion between the nozzle plate and substrate when the nozzle plate is an alcohol coated polymer, such as a polyimide nozzle plate coated with phenolic butyral.
  • FIG. 1 is a cross-sectional view of an ink jet print head containing a radiation cured resin composition according to the invention.
  • This invention relates to an ink jet print head having ink passage ways formed in a radiation cured resin layer which is attached to a substrate.
  • the passageways are connected in fluid flow communication to an ink discharging outlet provided by an orifice plate.
  • a resin composition is exposed to a radiation source in a predetermined pattern to cure certain regions of resin layer while other regions which provide the passage ways remain uncured. The uncured regions are removed from the resin layer leaving the desired passage ways.
  • the resin composition to be used for forming the radiation curable layers is a resin composition comprising: a first multifunctional epoxy compound, a second multifunctional epoxy compound, a photoinitiator capable of generating a cation, and a non photoreactive solvent.
  • the resin composition further comprises a film enhancing agent such as an acrylate or methacrylate polymer, as well as a silane having a functional group capable of reacting with at least one member selected from the group consisting of the first multifunctional epoxy compound, the second multifunctional epoxy compound and the photoinitiator.
  • a silane is preferably a silane with an epoxide functional group such as a glycidoxyalkyltrialkoxy-silane like gamma-glycidoxypropyltrimethoxy-silane.
  • the silane is present in an amount from about 0.05 to about 10 weight percent and preferably from about 0.1 to about 2.0 weight percent based on total weight of the resin composition, including all ranges subsumed therein.
  • Film enhancing agent as used herein, is defined to mean an organic material soluble in the resin composition which assists the film forming characteristics of the resin composition.
  • the amount of second multifunctional epoxy compound employed is less than about 4.5% and preferably less than about 4.0%.
  • the first component of the resin composition is a first multifunctional epoxy compound which includes any organic compound having preferably at least two oxirane rings polymerizable by ring opening. Therefore, multifunctional means having an average epoxide functionality of greater than 1.0 and preferably greater than or equal to 2. It is further noted that the first multifunctional epoxy compound and/or the second multifunctional epoxy compound may polymerize and/or crosslink. Preferably, the second multifunctional epoxy compound is the primary crosslinking agent.
  • the first multifunctional epoxy compound is preferably a difunctional epoxy compound which includes monomeric difunctional epoxy compounds and polymeric difunctional epoxy compounds which may vary in the nature of their backbone and substituent groups. Furthermore, the first multifunctional epoxy compound preferably has a hydroxy group as a substituent.
  • the molecular weight (M N ) of the first multifunctional epoxy compounds may vary from about 75 to about 100,000.
  • the difunctional epoxy compound or mixture of difunctional epoxy compounds are preferably liquids, however, one or more solid difunctional epoxy compounds may be included in the mixture provided that the final mixture is in a liquid phase.
  • Difunctional epoxy compounds which may be used include diglycidyl ethers of Bisphenol A (e.g. those available under the trade designations "Epon 828", “Epon 1004", “Epon 1001F”, “Epon SU-8” and “Epon 1010” from Shell Chemical Co., "DER-331", “DER-332", and “DER-334" from Dow Chemical Co.), 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexene carboxylate (e.g. "ERL-4221” from Union Carbide Corp.), 3,4-epoxy-6-methylcyclohexylmethyl-3,4-epoxy-6-methylcyclohexene carboxylate (e.g.
  • the difunctional epoxy compound is present in the composition in an amount of from about 5 to about 50 weight percent, preferably from about 10 to about 20 weight percent.
  • the second component of the resin composition is a second multifunctional epoxy compound.
  • the second multifunctional epoxy compound preferably increases the crosslink density thereby increasing resolution and improving resistance to solvent swelling.
  • the type of second multifunctional epoxy compound is generally not limited, as long as it is a compound capable of resulting in the desired resin.
  • An illustrative list of such second multifunctional epoxy compound includes, for example, those which are the reaction product of phenol; aldehydes and epoxides like DEN-431, DEN-438, DEN 439 (commercially available from Dow Plastics).
  • the second multifunctional epoxy compound is present in the composition in an amount of from about 0.5 to about 20 weight percent, preferably from about 1 to about 10 weight percent and most preferably from about 1 to about 5 weight percent, based on the total weight of the resin composition.
  • compound is meant to include monomers and polymers.
  • the third component of the resin composition is a photoinitiator capable of generating a cation such as an aromatic complex salt photoinitiator which may be selected from onium salts of a Group VA element, onium salts of a Group VIA element, and aromatic halonium salts. These complex salts, upon being exposed to ultraviolet radiation or electron beam irradiation, are capable of generating moieties which initiate reactions with epoxides.
  • the aromatic complex salt aromatic complex salt photoinitiator is present in the compositions in an amount of from about 1.0 to about 10 weight percent, preferably from about 1.5 to about 5 weight percent, based on the total weight of the resin composition.
  • Preferred aromatic complex salt photoinitiators include aromatic iodonium complex salts and aromatic sulfonium complex salts.
  • aromatic iodonium complex salt aromatic complex salt photoinitiators include:
  • the preferred salts are the diaryliodonium hexafluorophosphate and the diaryliodonium hexafluoroantimonate. These salts are preferred because, in general, they are more thermally stable, promote faster reaction, and are more soluble in inert organic solvents than are other aromatic iodonium salts of complex ions.
  • aromatic sulfonium complex salt aromatic complex salt photoinitiators examples include:
  • the preferred salts are the triaryl-substituted salts such as triphenylsulfonium hexafluorophosphate.
  • the triaryl-substituted salts are preferred because they are more thermally stable than the mono- and diaryl substituted salts thereby providing a one-part system with long shelf life.
  • the triaryl-substituted complex salts are also more amenable to dye sensitization. Consequently, the use of such complex salts results in compositions which are much more useful in applications where near ultraviolet and visible light are used for exposure.
  • the composition may be prepared in shelf stable concentrate form (i.e. with high levels of complex salt) which is suitable for later dilution to a more commercially practical coating composition.
  • the most preferred photoinitiator capable of generating a cation is a mixed triarylsulfonium hexafluoroantimonate salt, commercially available from Union Carbide (UVI-6974).
  • the fourth component of the resin composition is a nonphotoreactive solvent.
  • This solvent is limited only to the extent that the desired components, prior to curing are soluble in it.
  • Preferred nonphotoreactive solvents include gamma-butyrolactone, C 1-6 acetates, tetrahydrofuran, low molecular weight ketones, mixtures thereof and the like.
  • the nonphotoreactive solvent is present in the composition an amount of from about 20 to about 90 weight percent, preferably from about 45 to about 75 weight percent, based on the total weight of the resin composition.
  • the resin composition of the present invention may include up to about 35 weight percent and preferably about 10 to about 20 weight percent of an acrylate or methacrylate polymer which is derived from at least one acrylate or methacrylate monomer.
  • the polymer may be a homopolymer, a copolymer, or a blend.
  • the term "polymer” as used herein is meant to include oligomers (e.g. materials having a number average molecular weight as low as about 1000) as well as high polymers (which may have a number average molecular weight ranging up to about 1,000,000).
  • the number average molecular weight of the acrylate or methacrylate polymer is in the range of from about 10,000 to about 60,000 and most preferably from about 20,000 to about 30,000.
  • Preferred acrylate or methacrylate polymers may be derived from various monomers so long as at least one of those monomers is an acrylate or methacrylate monomer.
  • representative useful acrylate and methacrylate monomers include: methylmethacrylate, n-butylacrylate, hydroxyethylacrylate, hydroxyethylmethacrylate, n-butylmethacrylate, hydroxypropylacrylate, hydroxypropylmethacrylate, and ethylacrylate.
  • the acrylate and methacrylate monomers are esters of acrylic, or methacrylic, acid with an aliphatic alcohol of 1 to 4 carbon atoms or an aliphatic diol of 2 to 4 carbon atoms.
  • Representative useful acrylate or methacrylate polymers derived from the foregoing monomers include: methylmethacrylate/styrene/n-butylacrylate/hydroxyethylacrylate, methylmethacrylate/n-butylmethacrylate/hydroxyethylmethacrylate, and methylmethacrylate/n-butylmethacrylate.
  • the backbone of the acrylate or methacrylate polymer contains a major amount (by weight) of acrylate or methacrylate constituents while non-acrylate constituents, if any, represent a minor portion of the backbone.
  • acrylate or methacrylate polymers include "Elvacite 2008”, “Elvacite” 2013 (available from ICI Acrylics) which is methylmethacrylate(73)/n-butylmethacrylate(27) copolymer; “B-48N” (available from Rohm and Haas) which is an acrylic polymer; “lonac X-208” (available from lonac Chemical Company) which is a methylmethacrylate(44)/n-butylmethacrylate(45)/hydroxyethylacrylate(11) copolymer; “QR-572” (available from Rohm and Haas) which is a n-butylacrylate(80)/hydroxyethylacrylate(15)/vinyl acetate(5) copolymer; and “G-Cure 868” (available from General Mills) which is a methylmethacrylate(30)/n-butylacrylate(50)/hydroxyethylacrylate(20) copo
  • the resin composition of the invention may also contain various additives such as conventional fillers (e.g. barium sulfate, talc, glass bubbles) viscosity modifiers (e.g. pyrogenic silica), pigments, etc.
  • conventional fillers e.g. barium sulfate, talc, glass bubbles
  • viscosity modifiers e.g. pyrogenic silica
  • pigments etc.
  • the composition contains from about 45 to about 75 weight percent gamma-butyrolactone, from about 10 to about 20 weight percent first multifunctional epoxy compound, from about 0.1 to about 5.0 weight percent of a second multifunctional epoxy compound, from about 1.5 to about 5 weight percent of an aromatic complex salt photoinitiator, and from about 0.1 to about 2 weight percent gamma glycidoxypropyltrimethoxy-silane.
  • the composition contains from about 45 to about 75 weight percent gamma-butyrolactone, from about 10 to about 20 weight percent polymethyl methacrylate-co-methacrylic acid, from about 10 to about 20 weight percent first functional epoxy compound, from about 0.1 to about 5.0% by weight second multifunctional epoxy compound, from about 1.5 to about 3.0 weight percent aromatic complex salt photoinitiator, and from about 0.1 to about 2 weight percent gamma glycidoxypropyltrimethoxy-silane.
  • a method for applying the composition to a substrate involves centering the substrate on an appropriate sized chuck of either a resist spinner or conventional wafer resist deposition track.
  • the composition is either dispensed by hand or mechanically into the center of the substrate.
  • the chuck holding the substrate is then rotated at a predetermined number of revolutions per minute to evenly spread the composition from the center of the substrate to the edge of the substrate.
  • the rotational speed of the substrate may be adjusted or the viscosity of the material may be altered to vary the resulting film thickness.
  • the resulting coated substrate is then removed from the chuck either manually or mechanically and placed on either a temperature controlled hotplate or in a temperature controlled oven until the material is "soft" baked. This step removes a portion of the solvent from the liquid resulting in a partially dried film on the substrate.
  • the substrate is removed from the heat source and allowed to cool to room temperature.
  • the material In order to define patterns in the resulting film, the material must be masked, exposed to a collimated ultraviolet light source, baked after exposure and developed to define the final pattern by removing unneeded material.
  • This procedure is very similar to a standard semiconductor lithographic process.
  • the mask is a clear, flat substrate usually glass or quartz with opaque areas defining the pattern to be removed from the coated film (i.e. negative acting photoresist). The opaque areas prevent the ultraviolet light from cross linking the film masked beneath it.
  • the non-cross linked material is then solubilized by a developer and removed leaving the predetermined pattern behind on the substrate.
  • Illustrative developers include, for example, a xylene and butyl cellosolve acetate mixture and C 1-6 acetates like butyl acetate.
  • Curing of the resin composition of the invention occurs on exposure of the composition to any suitable source of radiation emitting actinic radiation at a wavelength within the ultraviolet and visible spectral regions. Exposures may be from less than about 1 second to 10 minutes or more depending upon the amounts of particular epoxy materials and aromatic complex salts being utilized and depending upon the radiation source and distance from the source and the thickness of the resist pattern to be hardened. The resin compositions may also be hardened by exposure to electron beam irradiation.
  • the substrate of the ink jet print head containing the energy imparting devices is a dielectric layer made from glass, metal, ceramic, or silicon.
  • the hardening is a triggered reaction, i.e. once the degradation of the aromatic complex salt has been initiated by exposure to a radiation source, the hardening reaction proceeds and will continue after the radiation source is removed.
  • the use of thermal energy during or after exposure to a radiation source will generally accelerate the hardening reaction, and even a moderate increase in temperature may greatly accelerate hardening rate.
  • the resin compositions of the invention are prepared, for example, by simply mixing the first and second multifunctional epoxy compounds, silane, acrylates, and non photoreactive solvent under conditions which do not promote curing. Once the resin mixture is prepared it is coated, for instance, onto an ink jet print head substrate by a coating technique known in the art such as spin coating, spraying, roll coating, and the like.
  • FIG. 1 is a schematic illustration of the ink jet print head of the invention.
  • the ink jet print head comprises a substrate 2, a radiation cured resin layer 4 on the substrate, an ink ejection chamber 10, an orifice 12, and a passage way 6.
  • the passage way 6 is in fluid flow communication with the orifice 12.
  • Orifice 12 is in nozzle plate 16, which is bonded to resin layer.
  • the print head contains an energy imparting device 18 for discharging the ink through the orifice 12.
  • the energy for discharging the ink is generated by applying electronic signals to the energy imparting device 18 as desired.
  • These energy imparting devices include heat resistance elements or piezoelectric elements which are arranged in predetermined patterns on the substrate 2.
  • ELVACITE 2008 is a low molecular weight polymethylmethacrylate (comprising 2-3% carboxylic acid functionality) which is a nonphotoreactive, impact absorbing binder that exhibits excellent film forming capabilities as well as providing the good thermal tack and adhesion needed for thermal compression bonding.
  • ELVACITE 2008 is available from ICI Acrylics.
  • EPON 1001F is a difunctional epoxy compound which adds to the tensile strength and to the elastomeric properties of the spun on film. EPON 1001F is available from Shell Chemical Company.
  • DEN 431 is a multifunctional epoxy resin that increases crosslink density thereby increasing resolution and improving the resistance to solvent swelling. DEN 431 is available from Dow Chemical Company.
  • Cyracure UVI 6974 is a aromatic complex salt photoinitiator allowing for the definition of patterns in the film when UV light is shown through an optical mask onto a film below. The resulting images are defined by developing away the uncrosslinked film leaving behind high resolution images in the epoxy thick film.
  • a 50 g/50 g solution of ELVACITE 2008 in gamma-butyrolactone was prepared. The mixture was turned for 16 hours on a roller mill. EPON 1001F, 40 grams, was crushed to a powder and added to the solution. The solution was turned for 16 hours on a roller mill. DEN 431, 10 grams, and 5 grams limonene oxide (a low viscosity liquid monofunctional epoxy) were added to the solution and mixed until the solution was homogeneous. UVI 6974, 10 grams, was added and mixed thoroughly.
  • the solution was spun onto a substrate used to make a printhead for an inkjet printer by means of a silicon wafer in a spinner at 2.5K rpm for 30 seconds to provide a 30 micron film which was subsequently developed. After this an inkjet nozzle plate was attached to the substrate by a conventional adhesion technique to produce an inkjet printhead. After placing the inkjet printhead in a conventional ink jet ink (at 60° C.), the nozzle plate began to detach after about 1 month.
  • a 50 g/50 g solution of ELVACITE 2008 in gamma-butyrolactone was prepared. The mixture was turned for 16 hours on a roller mill. EPON 1001F, 40 grams, was crushed to a powder and added to the solution. The solution was turned for 16 hours on a roller mill. DEN 431, 10 grams, was added to the solution and mixed until the solution was homogeneous. UVI 6974, 5 grams, was added and mixed thoroughly. To the resulting solution, 1 gram of glycidoxypropyltrimethoxy-silane was added.
  • the solution was spun onto a substrate used to make a printhead for an ink jet printer by means of a silicon wafer in a spinner at 2.5K rpm for 30 seconds to provide a 30 micron film which was developed.
  • a phenolic butyral coated polyimide ink jet nozzle plate was attached to the substrate by a conventional technique to produce an ink jet printhead. After placing the ink jet printhead in a conventional ink jet ink (at 60° C.), the nozzle plate did not, even remotely, begin to detach after about 1 month.

Landscapes

  • Manufacturing & Machinery (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Physics & Mathematics (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Epoxy Resins (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Particle Formation And Scattering Control In Inkjet Printers (AREA)
  • Polymerization Catalysts (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
US08/827,564 1997-03-28 1997-03-28 Ink jet print head containing a radiation curable resin layer Expired - Lifetime US5907333A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
US08/827,564 US5907333A (en) 1997-03-28 1997-03-28 Ink jet print head containing a radiation curable resin layer
DE69815189T DE69815189T2 (de) 1997-03-28 1998-03-27 Strahlungshärtbare Harzschicht enthaltender Tintenstrahldruckkopf
AT98302358T ATE242299T1 (de) 1997-03-28 1998-03-27 Strahlungshärtbare harzschicht enthaltender tintenstrahldruckkopf
CN98108878A CN1119245C (zh) 1997-03-28 1998-03-27 包含辐射固化树脂层的喷墨打印头
EP98302358A EP0867488B1 (en) 1997-03-28 1998-03-27 Ink jet print head containing a radiation curable resin layer
KR1019980010855A KR100527608B1 (ko) 1997-03-28 1998-03-28 방사선경화성수지조성물및당해조성물로이루어진방사선경화성수지층을함유하는잉크젯프린트헤드
JP12383498A JP4051467B2 (ja) 1997-03-28 1998-03-30 放射線硬化性樹脂層を備えたインク・ジェット・プリントヘッド
TW087104671A TW412633B (en) 1997-03-28 1998-06-23 Ink jet print head containing a radiation curable resin layer

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US08/827,564 US5907333A (en) 1997-03-28 1997-03-28 Ink jet print head containing a radiation curable resin layer

Publications (1)

Publication Number Publication Date
US5907333A true US5907333A (en) 1999-05-25

Family

ID=25249544

Family Applications (1)

Application Number Title Priority Date Filing Date
US08/827,564 Expired - Lifetime US5907333A (en) 1997-03-28 1997-03-28 Ink jet print head containing a radiation curable resin layer

Country Status (8)

Country Link
US (1) US5907333A (ko)
EP (1) EP0867488B1 (ko)
JP (1) JP4051467B2 (ko)
KR (1) KR100527608B1 (ko)
CN (1) CN1119245C (ko)
AT (1) ATE242299T1 (ko)
DE (1) DE69815189T2 (ko)
TW (1) TW412633B (ko)

Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999065687A1 (en) * 1998-06-15 1999-12-23 Lexmark International, Inc. Improved polymeric nozzle plate
US6151042A (en) * 1996-08-29 2000-11-21 Xerox Corporation High performance polymer compositions
US6158843A (en) * 1997-03-28 2000-12-12 Lexmark International, Inc. Ink jet printer nozzle plates with ink filtering projections
US6193359B1 (en) * 1998-04-21 2001-02-27 Lexmark International, Inc. Ink jet print head containing a radiation curable resin layer
US6283584B1 (en) 2000-04-18 2001-09-04 Lexmark International, Inc. Ink jet flow distribution system for ink jet printer
US6294317B1 (en) * 1999-07-14 2001-09-25 Xerox Corporation Patterned photoresist structures having features with high aspect ratios and method of forming such structures
US6322848B1 (en) * 1999-10-26 2001-11-27 Lord Corporation Flexible epoxy encapsulating material
US6327458B1 (en) 2000-04-06 2001-12-04 Lexmark International, Inc. Method and apparatus for positioning paper in an imaging system having an intermediate transfer medium
US6387719B1 (en) 2001-02-28 2002-05-14 Lexmark International, Inc. Method for improving adhesion
US6409316B1 (en) 2000-03-28 2002-06-25 Xerox Corporation Thermal ink jet printhead with crosslinked polymer layer
US20030170567A1 (en) * 2000-08-30 2003-09-11 Patil Girish S. Radiation curable resin layer
US20030207209A1 (en) * 2000-08-30 2003-11-06 Patil Girish S. Radiation curable resin layer
US20050203209A1 (en) * 2002-06-20 2005-09-15 Takahiro Furutani Pigment ink composition
US20050255409A1 (en) * 2004-05-14 2005-11-17 Park Byung-Ha Photo-curable resin composition, method of patterning the same, and ink jet head and method of fabricating the same
US20060001694A1 (en) * 2004-06-30 2006-01-05 Lexmark International, Inc Polyimide thickfilm flow feature photoresist and method of applying same
US20060221115A1 (en) * 2005-04-01 2006-10-05 Lexmark International, Inc. Methods for bonding radiation curable compositions to a substrate
US20070059531A1 (en) * 2005-09-13 2007-03-15 Park Byung-Ha Method of manufacturing inkjet printhead and inkjet printhead manufactured using the method
US20070076059A1 (en) * 2005-09-30 2007-04-05 Lexmark International, Inc Thick film layers and methods relating thereto
US20070087206A1 (en) * 2004-04-29 2007-04-19 Andrew Mclntosh Soutar UV Curable Coating Composition
US20070085881A1 (en) * 2004-08-19 2007-04-19 Cornell Robert W Methods for improved micro-fluid ejection devices
US20070092644A1 (en) * 2004-04-29 2007-04-26 Soutar Andrew M UV Curable Coating Composition
GB2423962B (en) * 2003-10-28 2008-01-09 Lexmark Int Inc Improved micro-fluid ejection devices and method therefor
US20080076197A1 (en) * 2006-09-04 2008-03-27 Canon Kabushiki Kaisha Method of manufacturing a liquid ejection head and liquid ejection head
US20090186293A1 (en) * 2008-01-23 2009-07-23 Bryan Thomas Fannin Dry film protoresist for a micro-fluid ejection head and method therefor
US7784917B2 (en) 2007-10-03 2010-08-31 Lexmark International, Inc. Process for making a micro-fluid ejection head structure
US20100328398A1 (en) * 2009-06-29 2010-12-30 Lambright Terry M Thermal inkjet print head with solvent resistance

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2253409C (en) * 1998-11-04 2003-06-17 Microjet Technology Co., Ltd. Method and device for manufacturing ink jet printhead
KR100469879B1 (ko) * 1999-12-10 2005-02-02 후지 샤신 필름 가부시기가이샤 잉크젯 헤드, 잉크젯 헤드의 제조 방법 및 인쇄 장치
DE10328525B4 (de) * 2003-06-24 2008-02-28 W.C. Heraeus Gmbh Verwendung von Siebdrucklacken bei der Herstellung von Abziehbildern zur Dekoration von keramischen Substraten, Porzellan und Glas
JP4646610B2 (ja) * 2004-12-01 2011-03-09 キヤノン株式会社 インクジェット記録ヘッド
KR100670004B1 (ko) 2005-02-25 2007-01-19 삼성전자주식회사 잉크젯 프린트헤드
JP5480388B2 (ja) * 2009-10-12 2014-04-23 ヒューレット−パッカード デベロップメント カンパニー エル．ピー． 圧電部材の欠陥の修復

Citations (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4090936A (en) * 1976-10-28 1978-05-23 Minnesota Mining And Manufacturing Company Photohardenable compositions
US4173476A (en) * 1978-02-08 1979-11-06 Minnesota Mining And Manufacturing Company Complex salt photoinitiator
US4297401A (en) * 1978-12-26 1981-10-27 Minnesota Mining & Manufacturing Company Liquid crystal display and photopolymerizable sealant therefor
US4392013A (en) * 1979-12-27 1983-07-05 Asahi Kasei Kogyo Kabushiki Kaisha Fine-patterned thick film conductor structure and manufacturing method thereof
US4401537A (en) * 1978-12-26 1983-08-30 Minnesota Mining And Manufacturing Company Liquid crystal display and photopolymerizable sealant therefor
US4609427A (en) * 1982-06-25 1986-09-02 Canon Kabushiki Kaisha Method for producing ink jet recording head
US4623676A (en) * 1985-01-18 1986-11-18 Minnesota Mining And Manufacturing Company Protective coating for phototools
US4666823A (en) * 1982-06-18 1987-05-19 Canon Kabushiki Kaisha Method for producing ink jet recording head
US4688053A (en) * 1985-07-13 1987-08-18 Canon Kabushiki Kaisha Liquid jet recording head having a layer of a resin composition curable with an active energy ray
US4688056A (en) * 1985-07-13 1987-08-18 Canon Kabushiki Kaisha Liquid jet recording head having a layer of a resin composition curable with an active energy ray
US4775445A (en) * 1984-12-28 1988-10-04 Canon Kabushiki Kaisha Process for producing a liquid jet recording head
US4948645A (en) * 1989-08-01 1990-08-14 Rogers Corporation Tape automated bonding and method of making the same
JPH0384026A (ja) * 1989-08-25 1991-04-09 Toyobo Co Ltd 電子部品封止用硬化型樹脂組成物
EP0432795A1 (en) * 1989-12-15 1991-06-19 Canon Kabushiki Kaisha Active energy-ray-curable resin composition, ink jet head having ink path wall formed by use of the composition, process for preparing the head, and ink-jet apparatus provided with the head
US5275695A (en) * 1992-12-18 1994-01-04 International Business Machines Corporation Process for generating beveled edges
US5290667A (en) * 1991-12-03 1994-03-01 Canon Kabushiki Kaisha Method for producing ink jet recording head
US5297331A (en) * 1992-04-03 1994-03-29 Hewlett-Packard Company Method for aligning a substrate with respect to orifices in an inkjet printhead
US5334999A (en) * 1990-10-18 1994-08-02 Canon Kabushiki Kaisha Device for preparing ink jet recording head with channels containing energy generating elements
US5478606A (en) * 1993-02-03 1995-12-26 Canon Kabushiki Kaisha Method of manufacturing ink jet recording head
US5578417A (en) * 1989-01-10 1996-11-26 Canon Kabushiki Kaisha Liquid jet recording head and recording apparatus having same
JPH091804A (ja) * 1995-06-21 1997-01-07 Canon Inc インクジェット記録ヘッドの製造方法および同方法により製造されたインクジェット記録ヘッド
JPH0924614A (ja) * 1995-07-11 1997-01-28 Canon Inc 液体噴射記録ヘッド用保護膜材料および該保護膜材料を用いた液体噴射記録ヘッドおよび液体噴射記録ヘッドキット

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4426431A (en) * 1982-09-22 1984-01-17 Eastman Kodak Company Radiation-curable compositions for restorative and/or protective treatment of photographic elements
JPH02113022A (ja) * 1988-10-20 1990-04-25 Yokohama Rubber Co Ltd:The 紫外線硬化型エポキシ樹脂組成物
KR910010027B1 (ko) * 1989-03-03 1991-12-10 동양나이론 주식회사 열가소성 수지 조성물

Patent Citations (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4090936A (en) * 1976-10-28 1978-05-23 Minnesota Mining And Manufacturing Company Photohardenable compositions
US4173476A (en) * 1978-02-08 1979-11-06 Minnesota Mining And Manufacturing Company Complex salt photoinitiator
US4297401A (en) * 1978-12-26 1981-10-27 Minnesota Mining & Manufacturing Company Liquid crystal display and photopolymerizable sealant therefor
US4401537A (en) * 1978-12-26 1983-08-30 Minnesota Mining And Manufacturing Company Liquid crystal display and photopolymerizable sealant therefor
US4392013A (en) * 1979-12-27 1983-07-05 Asahi Kasei Kogyo Kabushiki Kaisha Fine-patterned thick film conductor structure and manufacturing method thereof
US4666823A (en) * 1982-06-18 1987-05-19 Canon Kabushiki Kaisha Method for producing ink jet recording head
US4609427A (en) * 1982-06-25 1986-09-02 Canon Kabushiki Kaisha Method for producing ink jet recording head
US4775445A (en) * 1984-12-28 1988-10-04 Canon Kabushiki Kaisha Process for producing a liquid jet recording head
US4623676A (en) * 1985-01-18 1986-11-18 Minnesota Mining And Manufacturing Company Protective coating for phototools
US4688053A (en) * 1985-07-13 1987-08-18 Canon Kabushiki Kaisha Liquid jet recording head having a layer of a resin composition curable with an active energy ray
US4688056A (en) * 1985-07-13 1987-08-18 Canon Kabushiki Kaisha Liquid jet recording head having a layer of a resin composition curable with an active energy ray
US5578417A (en) * 1989-01-10 1996-11-26 Canon Kabushiki Kaisha Liquid jet recording head and recording apparatus having same
US4948645A (en) * 1989-08-01 1990-08-14 Rogers Corporation Tape automated bonding and method of making the same
JPH0384026A (ja) * 1989-08-25 1991-04-09 Toyobo Co Ltd 電子部品封止用硬化型樹脂組成物
EP0432795A1 (en) * 1989-12-15 1991-06-19 Canon Kabushiki Kaisha Active energy-ray-curable resin composition, ink jet head having ink path wall formed by use of the composition, process for preparing the head, and ink-jet apparatus provided with the head
US5334999A (en) * 1990-10-18 1994-08-02 Canon Kabushiki Kaisha Device for preparing ink jet recording head with channels containing energy generating elements
US5290667A (en) * 1991-12-03 1994-03-01 Canon Kabushiki Kaisha Method for producing ink jet recording head
US5297331A (en) * 1992-04-03 1994-03-29 Hewlett-Packard Company Method for aligning a substrate with respect to orifices in an inkjet printhead
US5275695A (en) * 1992-12-18 1994-01-04 International Business Machines Corporation Process for generating beveled edges
US5478606A (en) * 1993-02-03 1995-12-26 Canon Kabushiki Kaisha Method of manufacturing ink jet recording head
JPH091804A (ja) * 1995-06-21 1997-01-07 Canon Inc インクジェット記録ヘッドの製造方法および同方法により製造されたインクジェット記録ヘッド
JPH0924614A (ja) * 1995-07-11 1997-01-28 Canon Inc 液体噴射記録ヘッド用保護膜材料および該保護膜材料を用いた液体噴射記録ヘッドおよび液体噴射記録ヘッドキット

Cited By (47)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6323301B1 (en) 1996-08-29 2001-11-27 Xerox Corporation High performance UV and heat crosslinked or chain extended polymers
US6151042A (en) * 1996-08-29 2000-11-21 Xerox Corporation High performance polymer compositions
US6158843A (en) * 1997-03-28 2000-12-12 Lexmark International, Inc. Ink jet printer nozzle plates with ink filtering projections
US6193359B1 (en) * 1998-04-21 2001-02-27 Lexmark International, Inc. Ink jet print head containing a radiation curable resin layer
US6371600B1 (en) * 1998-06-15 2002-04-16 Lexmark International, Inc. Polymeric nozzle plate
WO1999065687A1 (en) * 1998-06-15 1999-12-23 Lexmark International, Inc. Improved polymeric nozzle plate
US6294317B1 (en) * 1999-07-14 2001-09-25 Xerox Corporation Patterned photoresist structures having features with high aspect ratios and method of forming such structures
US6322848B1 (en) * 1999-10-26 2001-11-27 Lord Corporation Flexible epoxy encapsulating material
US6409316B1 (en) 2000-03-28 2002-06-25 Xerox Corporation Thermal ink jet printhead with crosslinked polymer layer
US6327458B1 (en) 2000-04-06 2001-12-04 Lexmark International, Inc. Method and apparatus for positioning paper in an imaging system having an intermediate transfer medium
US6283584B1 (en) 2000-04-18 2001-09-04 Lexmark International, Inc. Ink jet flow distribution system for ink jet printer
US6783918B2 (en) * 2000-08-30 2004-08-31 Lexmark International, Inc. Radiation curable resin layer
US6830646B2 (en) * 2000-08-30 2004-12-14 Lexmark International, Inc. Radiation curable resin layer
US20030170567A1 (en) * 2000-08-30 2003-09-11 Patil Girish S. Radiation curable resin layer
US20030207209A1 (en) * 2000-08-30 2003-11-06 Patil Girish S. Radiation curable resin layer
US6550893B2 (en) * 2001-02-28 2003-04-22 Lexmark International, Inc. Semiconductor chip for an ink jet printhead and method for making same
US6387719B1 (en) 2001-02-28 2002-05-14 Lexmark International, Inc. Method for improving adhesion
US20050203209A1 (en) * 2002-06-20 2005-09-15 Takahiro Furutani Pigment ink composition
US20080234428A1 (en) * 2002-06-20 2008-09-25 Takahiro Furutani Pigmented ink composition
US7393884B2 (en) * 2002-06-20 2008-07-01 Hitachi Maxwell, Ltd. Pigment ink composition
WO2004092237A2 (en) * 2003-04-14 2004-10-28 Lexmark International, Inc. Radiation curable resin layer
WO2004092237A3 (en) * 2003-04-14 2005-04-14 Lexmark Int Inc Radiation curable resin layer
GB2423962B (en) * 2003-10-28 2008-01-09 Lexmark Int Inc Improved micro-fluid ejection devices and method therefor
US20070092644A1 (en) * 2004-04-29 2007-04-26 Soutar Andrew M UV Curable Coating Composition
US7594718B2 (en) * 2004-04-29 2009-09-29 Hewlett-Packard Development Company, L.P. UV curable coating composition
US7306315B2 (en) * 2004-04-29 2007-12-11 Hewlett-Packard Development Company, L.P. UV curable coating composition
US20070087206A1 (en) * 2004-04-29 2007-04-19 Andrew Mclntosh Soutar UV Curable Coating Composition
US20080063978A1 (en) * 2004-05-14 2008-03-13 Park Byung-Ha Photo-curable resin composition, method of patterning the same, and ink jet head and method of fabricating the same
US20050255409A1 (en) * 2004-05-14 2005-11-17 Park Byung-Ha Photo-curable resin composition, method of patterning the same, and ink jet head and method of fabricating the same
US7278709B2 (en) * 2004-05-14 2007-10-09 Samsung Electronics Co., Ltd. Photo-curable resin composition, method of patterning the same, and ink jet head and method of fabricating the same
US20070188552A1 (en) * 2004-06-30 2007-08-16 Bertelsen Craig M Polyimide thickfilm flow feature photoresist and method of applying same
US7204574B2 (en) 2004-06-30 2007-04-17 Lexmark International, Inc. Polyimide thickfilm flow feature photoresist and method of applying same
US20060001694A1 (en) * 2004-06-30 2006-01-05 Lexmark International, Inc Polyimide thickfilm flow feature photoresist and method of applying same
US20070085881A1 (en) * 2004-08-19 2007-04-19 Cornell Robert W Methods for improved micro-fluid ejection devices
US20060221115A1 (en) * 2005-04-01 2006-10-05 Lexmark International, Inc. Methods for bonding radiation curable compositions to a substrate
US20070059531A1 (en) * 2005-09-13 2007-03-15 Park Byung-Ha Method of manufacturing inkjet printhead and inkjet printhead manufactured using the method
US7854493B2 (en) 2005-09-13 2010-12-21 Samsung Electronics Co., Ltd. Method of manufacturing inkjet printhead and inkjet printhead manufactured using the method
US20070076059A1 (en) * 2005-09-30 2007-04-05 Lexmark International, Inc Thick film layers and methods relating thereto
US7571979B2 (en) 2005-09-30 2009-08-11 Lexmark International, Inc. Thick film layers and methods relating thereto
US20090269707A1 (en) * 2005-09-30 2009-10-29 Lexmark International, Inc. Thick Film Layers and Methods Relating Thereto
US8007990B2 (en) 2005-09-30 2011-08-30 Lexmark International, Inc. Thick film layers and methods relating thereto
US20080076197A1 (en) * 2006-09-04 2008-03-27 Canon Kabushiki Kaisha Method of manufacturing a liquid ejection head and liquid ejection head
US8029685B2 (en) 2006-09-04 2011-10-04 Canon Kabushiki Kaisha Liquid ejection head and its method of manufacture
US7784917B2 (en) 2007-10-03 2010-08-31 Lexmark International, Inc. Process for making a micro-fluid ejection head structure
US20090186293A1 (en) * 2008-01-23 2009-07-23 Bryan Thomas Fannin Dry film protoresist for a micro-fluid ejection head and method therefor
US20100328398A1 (en) * 2009-06-29 2010-12-30 Lambright Terry M Thermal inkjet print head with solvent resistance
US8454149B2 (en) 2009-06-29 2013-06-04 Videojet Technologies Inc Thermal inkjet print head with solvent resistance

Also Published As

Publication number Publication date
DE69815189D1 (de) 2003-07-10
CN1119245C (zh) 2003-08-27
KR19980080815A (ko) 1998-11-25
CN1197817A (zh) 1998-11-04
KR100527608B1 (ko) 2006-02-28
JP4051467B2 (ja) 2008-02-27
EP0867488A1 (en) 1998-09-30
EP0867488B1 (en) 2003-06-04
TW412633B (en) 2000-11-21
ATE242299T1 (de) 2003-06-15
JPH10338798A (ja) 1998-12-22
DE69815189T2 (de) 2004-06-03

Similar Documents

Publication Publication Date Title
US5907333A (en) Ink jet print head containing a radiation curable resin layer
US6193359B1 (en) Ink jet print head containing a radiation curable resin layer
US7364268B2 (en) Nozzle members, compositions and methods for micro-fluid ejection heads
JP3143307B2 (ja) インクジェット記録ヘッドの製造方法
US7485412B2 (en) Ink jet head manufacturing method and ink jet head manufactured by the manufacturing method
US8173031B2 (en) Photoimageable nozzle members and methods relating thereto
EP1138494A2 (en) Ink jet printhead
US6895668B2 (en) Method of manufacturing an ink jet recording head
EP0734866A2 (en) Process for the production of an ink jet head
KR20070043805A (ko) 감광성 수지 조성물, 감광성 수지 조성물을 사용한 잉크젯헤드 및 잉크젯 헤드의 제조 방법
US8007990B2 (en) Thick film layers and methods relating thereto
US20060221115A1 (en) Methods for bonding radiation curable compositions to a substrate
JP3986060B2 (ja) インクジェット記録ヘッドの流路構成部材及びインクジェット記録ヘッドの製造方法
JP2001179990A (ja) インクジェット記録ヘッド及びその製造方法
US6982022B2 (en) Formation of photopatterned ink jet nozzle plates by transfer methods
US7423073B2 (en) Radiation curable compositions having improved flexibility
US11987052B2 (en) Photoimageable nozzle plate having increased solvent resistance
KR100670004B1 (ko) 잉크젯 프린트헤드
JP2005169846A (ja) 液体噴射記録ヘッドの製造方法、及び該製造工程における中間構造体

Legal Events

Date Code Title Description
AS Assignment

Owner name: LEXMARK INTERNATIONAL, INC., KENTUCKY

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:PATIL, GIRISH S.;SPIVEY, PAUL T.;WILLIAMS, GARY R.;REEL/FRAME:009130/0050

Effective date: 19971014

STCF Information on status: patent grant

Free format text: PATENTED CASE

FPAY Fee payment

Year of fee payment: 4

FPAY Fee payment

Year of fee payment: 8

FPAY Fee payment

Year of fee payment: 12

AS Assignment

Owner name: FUNAI ELECTRIC CO., LTD, JAPAN

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:LEXMARK INTERNATIONAL, INC.;LEXMARK INTERNATIONAL TECHNOLOGY, S.A.;REEL/FRAME:030416/0001

Effective date: 20130401